Syntheses and crystal structure of a (2,6-diisopropyldinaphtho[2,1-d:1′,2′-f][1,3]dithiepin-4-yl)(phenyl)methanol atropisomer

Abstract

The racemic title compound, C34H32OS2, comprises an atropisomeric binaphthyl dithioacetal substituted at the methylene carbon atom with a chiral benzyl alcohol. The two naphthalene ring systems are additionally substituted at the 3,3′-position with isopropyl groups. The overall stereochemistry is defined as aS,R and aR,S. The hydroxyl group forms an intramolecular O—H...S hydrogen bond to one of the sulfur atoms. The crystal structure contains weak C—H...π interactions that link the molecules into extended arrays.

Keywords

• crystal structure
• atropisomer
• binaphthalene dithiol
• asymmetric synthesis
• hydrogen bonds
• c—h...π contacts